Ortho-dioxyphenylethanolmethylamin and process of making same.



. aqueous solution.

UNITED P TENT" OFFICE.

FRIEDRICH STOLZ AND FRANZ FLAECHER, or HOOHST-QN-THE-MAIN, GERMANY,

ASSIGNORS, IIBY MESNE ASSIGNMENTS, TO H. A. METZ & co, A. COMPANY or NEW- YORK.

ORTHQ-DIOXYPHENYIETHANOLMETHYLAMILF AND PROCESS OF MAKING SAME.

To all whom it may concern:

Be it known that we, FRIEDRICH SToLz, Ph. D., and FRANZ FLAEGHER, Ph. 'D., chemists, citizens of the Empire of Germany, and residents of Hochst-on-the-Main, in said Empire of Germany, have invented certain new and useful Im rovements in Making Ortho Dioxypheny ethanolmethylamin, of which the following is .a description.

Our invention relates to certain new and useful improvements in astringent or hemostatic' products, as will be hereinafter more fully described.

It is well known that the suprarenal glands possess hemostatic, blood-pressureraising attributes, that these glands have been treated in various ways, and the active principle thereof utilized for a considerable period. The products obtained, however, have been more or less unsatisfactory by reason of their lack of purity and instability, and our invention consists in a new, synthetic product which possesses all of the valuable astringent and .blood-pressure-raising properties, and one which is stable, uniform, and reliable.

We have found that the alcohol bases produced by the reduction of amino, or alkylamino-aceto-pyrocatechol may be obtained in a substantially'pure state by extracting the acid solution resulting by reduction from the aforesaid keto bases, with a solvent, such, for instance, as etheror ethyl acetate, in order to eliminate any by-pr'oducts, and by then adding ammonia to the concentrated 'lhe'separated base may then be transformed into its oxalate which crystallizes from alcohol whence it may be regenerated.

The process is, for instance, as follows: Ten parts by weight of the hydrochlorid of methylamino aceto pyrocatechol are dissolved in 10 times the quantity of water and reduced by introducing 120 parts by weight of sodium amalgam while cooling. The solution is kept during the o cration feebly acid by dropping into it dilute hydrochloric acid. The aqueous ,solution thus obtained is repeatedly shaken out with ether and may hereafter be concentrated by evaporating in a vacuum; the separated sodium ehlorid may be filtered and the solution again extracted with ether. On adding ammonia until the solution reacts alkaline Specification of Letters Patent.

Patented AughlO, 1909.

Application filed September 7-, 1906. Serial No. 335,623. (Specimens) to curcuma, the dioxyphenylethanolmethylamm is precipitated as a crystalline powder. This base may be further transformed into its oxalate which crystallizes from alcohol ortho dioxyphenylethanolmethylamin thus obtained has the formula 0 H,(OH )-CH(OH)CH NHCH It forms a white crystalline powder of the rooted). It is soluble with great difficulty in water, alcohol and ether. When dry it is stable, contrary to'the roduct obtained by Dakin (Proceedings of tfie Chem. 800., 1905, p. 154) from methyIamin-aceto-pyrocatecholJ The hydrochlorid of the base is very easily alcohol. The aqueous solution of the salts yields a green colorwith ferric chlorid. No decomposition at all occurs on keeping the pure compound obtained according to this process and the physiological efficacy is preserved for a year and more. The roduct is used as an astringent or hemostatic, and as an addition to local anesthetics, preferably in the proportion of 1-20 drops of a solution of 1:1000 of the hydrochlorid of the compound. It may be applied subcutaneously or internally.

Having now described our invention, wha we claim is 1. As a new product, a substance derived from pyrocatechol arid possessing the hereindescribed astringent or hemostatic propertalline powder having a melting point of substantially 208 degrees C. and being diflicultly soluble in water, alcohol or ether, stable when in a dry state, and optically inactive.

2. As a new product, the ortho-dioxyphenylethanolmethylamin in a substantially pure state, consisting of a white crystalline )owder having a melting point of 208 degrees being difficultly soluble in water, alcohol or ether, stable when in a dry state, and optically inactive. I 3. The herein-described process consisting in reducing by means of an appropriate reducing reagent, a slightly acid, aqueous solution of the hydrochlorid of methyl-aminoaceto pyrocatechol, washing the said solution with an immiscible, volatile fluid for whence the base may be regenerated. The

melting point of 208 degrees C. (not cor-J ties, consisting of a substantially white crys-- soluble, but the. oxalate crystallizes from the removal of impurities, concentrating in :1 vacuum, removing sodium clilorid, and precipitating the salt by means of appropriate reagents.

4. The herein-described process Wliiclreonsis ts in dissolving the hydrochlorid of methyl- :unino-aceto-pyrocntechol in slightly ec-idulnteil Water, reducing said llyilrochlorid by introihicing sodium inna-lgmn into the solution, shaking out the solution with other to extract by-products, concentrating the solution, filtering the some to remove sodium chlorid, again extracting the solution with I ether, andedding ammonia, to the solution I to qreoipitate ortho (lioxyphenylethunol- 1 met iylemin.

i In testimony, that we claim the foregoing as our invention, we have signed our names in presence of two subscribing witnesses.

, FlillQDlilUll STOLZ.

l FRANZ FLAECIHCR.

E VY'itnesses:

i JEAN 11mm),

1 CARL G'RUND. 

